Tetrahydrofuran → N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamide

HRID 1694957Notes

Reaction equation

HRID 1694957 reaction equation
C(N(CC)CC)C.[CH:8]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[C:11]([S:17](Cl)(=[O:19])=[O:18])=[CH:10][CH:9]=1.Cl.[NH2:22][C@H:23]([C@H:26]1[O:30][C:29](=[O:31])[C@H:28]([CH3:32])[CH2:27]1)[CH2:24][OH:25].O1CCCC1>O>[OH:25][CH2:24][C@H:23]([NH:22][S:17]([C:11]1[CH:10]=[CH:9][CH:8]=[CH:13][C:12]=1[N+:14]([O-:16])=[O:15])(=[O:19])=[O:18])[C@@H:26]1[CH2:27][C@@H:28]([CH3:32])[C:29](=[O:31])[O:30]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 155402-Nitrobenzenesulfonyl chlorideHCID 66645577(3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-methyldihydrofuran-2-one hydrochloride

Product 1

HCID 66645672N-{(S)-2-hydroxy-1-[(2S,4R)-4-methyl-5-oxotetrahydrofuran-2-yl]ethyl}-2-nitrobenzenesulfonamideYield 56%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.66 g of triethylamine (85.7 mmol) and 9.67 g of O-nitrobenzenesulfonyl chloride (41.3 mmol) were added to a solution of (3R,5S)-5-[(S)-1-amino-2-hydroxyethyl]-3-methyldihydrofuran-2-one hydrochloride obtained in the above reaction in a mixed solvent of tetrahydrofuran (120 ml) and water (12.0 ml) at 0° C., and the mixture was stirred at the same temperature for two hours. The reaction mixture was concentrated under reduced pressure and 200 ml of water was added, followed by extraction with ethyl acetate. Then, the organic layer was washed with water, a saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent:ethyl acetate). Further, 10 ml of diisopropyl ether and 20 ml of ethyl acetate were added, and the precipitated solid was collected by filtration to obtain 5.27 g of the title compound (total yield over two steps: 56%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and 200 ml of water
  2. additionwas added
  3. extractionfollowed by extraction with ethyl acetate
  4. washThen, the organic layer was washed with water
  5. dry with materiala saturated sodium bicarbonate aqueous solution and brine and dried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (elution solvent:ethyl acetate)
  9. additionFurther, 10 ml of diisopropyl ether and 20 ml of ethyl acetate were added
  10. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ded480ffa9fc4fa39f462a4d5849e77f
Source dataset
uspto-grants-2012_04
Patent number
US08158790B2

Reaction notes

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